John Sayles isn’t about typical. He isn’t about routine, either, and although Baby It’s You was his first film to be backed by a major studio (and his third overall), it’s far from just another conventional high school love story.

Jill (Rosanna Arquette) is a high school girl in Trenton, New Jersey in 1966, a middle-class girl who’s smart, popular, and longs to become an actress. Up comes a good-looking Italian guy from the wrong side of the tracks, a boy calling himself Sheik (Vincent Spano) who dresses well and wants to be Frank Sinatra. (His favorite people, he claims, are Jesus Christ, Sinatra, and himself. No confidence issues here…)

We’ve seen this set-up so many times, we know exactly what’s going to happen: a rocky start to the relationship, friends and parents who don’t understand, problems at school, the list goes on. But I’ll say it again: Sayles isn’t about typical, and although some of the situations in Baby It’s You may look familiar, Sayles makes them feel fresh, mostly by giving his characters dialogue and reactions that aren’t the same tired clichés we’ve heard before. Spano brings a convincing confidence to Sheik, but it’s Arquette who propels the film forward, portraying Jill as a girl with the drive to succeed, yet at the same time vulnerable to the changes going on around her as she seeks to find the right college for acting. Sheik initially inspires revulsion, then curiosity, then confusion, all of which Arquette pulls off convincingly.

Baby It’s You is essentially a film in two parts.The first half focuses on Jill’s last year of high school; the second, her first year at Sarah Lawrence College. Although we’re probably only talking a span of a year or two in narrative, the two settings seem worlds apart, with Jill’s high school days feeling more like the 50s and college life closer to the later 60s. I think that’s one of Sayles’s points. Jill has gone to another world, and while Sheik has left Trenton to work in a Miami nightclub (lip-syncing Frank Sinatra records), he really hasn’t changed much. When they meet up again, Jill recognizes this; Sheik doesn’t.

The first half of the film will probably appeal more to most audiences than the second half. It’s a more traditional narrative, sort of a period piece of ill-fated romance, yet far from typical. Initially the second half of the film doesn’t seem to work, but in fact it does. Jill realizes that the things that came easily in high school don’t really give her much of an advantage in college. We see her go through a transformation, but a transformation that’s incomplete. She’s not sure where she’s going or what she wants, but she knows where Sheik fits it – or doesn’t. The ending of the film may seem unrealistic and confusing, but consider the lives of people making the transition from high school to college and adulthood. Wasn’t that an unrealistic and confusing time? Sayles understands this and that knowledge elevates Baby It’s You beyond typical teenage fare to something that requires reflection and consideration. Not all of it works all the time, but enough of it does to make it worth watching.

Sayles is responsible for two of my favorite films from the 90s, Passion Fish (1992) and Lone Star (1996), but this is the earliest of his films that I’ve seen. Like those films, Baby It’s You challenges you to get inside its characters, feel what they feel, see the world through their eyes, and reflect on your own life. Unfortunately not too many directors can do that.